Nope, though he could be seen wearing a fedora on very cold Winter days in Chicago but that was back when he would walk a mile or so from his office to the health club; before he entered the Senate and began being chauffeured around in town cars.J B said:Regarding President Obama, has he even been seen donning a brimmed hat since he wore that black cowboy hat
If memory serves, he wore something like this; brown, self banded, probably wool, less the pin and feather. A relatively common hat for Chicago pols.